4'-Deaza-1'-Aza-2'-Deoxy-1'-(9-Methylene)-Immucillin-H, (3r,4r)-N-[9-Deazahypoxanthin-9-Yl)Methyl]-4-Hydroxymethyl-Pyrrolidin-3-Ol

Identification

Name
4'-Deaza-1'-Aza-2'-Deoxy-1'-(9-Methylene)-Immucillin-H, (3r,4r)-N-[9-Deazahypoxanthin-9-Yl)Methyl]-4-Hydroxymethyl-Pyrrolidin-3-Ol
Accession Number
DB03551  (EXPT01206)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 267.3043
Monoisotopic: 267.145715494
Chemical Formula
C12H19N4O3
InChI Key
WFVGWLHAOKEIOJ-MFQSTILNSA-O
InChI
InChI=1S/C12H18N4O3/c17-5-8-3-16(4-9(8)18)2-7-1-13-11-10(7)14-6-15-12(11)19/h1,6,8-11,13,17-18H,2-5H2,(H,14,15,19)/p+1/t8-,9+,10?,11?/m1/s1
IUPAC Name
4-hydroxy-7-{[(3R,4R)-3-hydroxy-4-(hydroxymethyl)pyrrolidin-1-yl]methyl}-4aH,5H,7aH-pyrrolo[3,2-d]pyrimidin-5-ium
SMILES
[H][[email protected]]1(O)CN(CC2=C[NH2+]C3([H])C(O)=NC=NC23[H])C[[email protected]]1([H])CO

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPurine nucleoside phosphorylaseNot AvailableHuman
UPurine nucleoside phosphorylaseNot AvailableMycobacterium tuberculosis
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
131704253
PubChem Substance
46506720
ChemSpider
4450306
HET
DIH
PDB Entries
1n3i / 1rsz / 2a0w / 2a0x / 2a0y / 2p4s / 3bgs / 3occ / 3of3

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.616 mg/mLALOGPS
logP-1.5ALOGPS
logP-5ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)5.42ChemAxon
pKa (Strongest Basic)8.66ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area105.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.52 m3·mol-1ChemAxon
Polarizability26.93 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9345
Blood Brain Barrier-0.6745
Caco-2 permeable-0.6911
P-glycoprotein substrateSubstrate0.8241
P-glycoprotein inhibitor INon-inhibitor0.734
P-glycoprotein inhibitor IINon-inhibitor0.9153
Renal organic cation transporterNon-inhibitor0.7605
CYP450 2C9 substrateNon-substrate0.8327
CYP450 2D6 substrateNon-substrate0.7946
CYP450 3A4 substrateNon-substrate0.5282
CYP450 1A2 substrateNon-inhibitor0.7432
CYP450 2C9 inhibitorNon-inhibitor0.9079
CYP450 2D6 inhibitorNon-inhibitor0.9143
CYP450 2C19 inhibitorNon-inhibitor0.8516
CYP450 3A4 inhibitorNon-inhibitor0.9945
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9692
Ames testNon AMES toxic0.646
CarcinogenicityNon-carcinogens0.9014
BiodegradationNot ready biodegradable0.8977
Rat acute toxicity2.5735 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8278
hERG inhibition (predictor II)Non-inhibitor0.755
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Pyrrolopyrimidines / Hydropyrimidines / N-alkylpyrrolidines / 1,3-aminoalcohols / Pyrroles / Pyrrolines / Quaternary ammonium salts / Secondary alcohols / Trialkylamines / 1,2-aminoalcohols
show 11 more
Substituents
Alpha-amino acid or derivatives / Pyrrolopyrimidine / Hydropyrimidine / 1,4,5,6-tetrahydropyrimidine / N-alkylpyrrolidine / 1,3-aminoalcohol / Pyrrole / Pyrrolidine / Pyrroline / Quaternary ammonium salt
show 25 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Purine-nucleoside phosphorylase activity
Specific Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine ...
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
The purine nucleoside phosphorylases catalyze the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate. Cleaves guanosine, inosine, 2'-deoxyguanosine and 2'-deoxyinosine.
Specific Function
Purine-nucleoside phosphorylase activity
Gene Name
punA
Uniprot ID
P9WP01
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
27571.215 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:15